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Synthesis and Reactions of 3-Phenyl-3,4-Dihydro-1, 4-Quinoxalin-2 (1H) -One and its Heterocyclic Analogues

✍ Scribed by T. O. Olagbemiro; C. A. Nyakutse; L. Lajide; M. O. Agho; C. E. Chukwu

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
333 KB
Volume
96
Category
Article
ISSN
0037-9646

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✦ Synopsis

were synthesized by reactions o? methyl 2-bromo-2-phmylethanorrte 1 with oFthosubstituted arylaminea 2a -2c. Subsequent reductive alkylationofthe lactams with aodium hydride and-iodobthane afforded only the N-alkylated quinoxalinone 4a and benzothiazinone 4b. Lithium aluminium hydride reduction of the lactams 3 8 -3 ~ gave the dihydro-aerivatives 5a, 5b and 5c while similar reduction of the A-aIkylated lactams 4a and 4b yieldzd tlie unsafurated quinoxaline 6a and benzothiazine 6b respectively. Lead tetraacetate oxidation of the quinsxalinone 3a furnished-the unsaturated quinoxalinone 9 which was N-alkylated using sodiumborohydride in formic acid to give 10. Treatment of the 1actm.w 3a, 3b and 3c with phosphorus pentasulphide produGd only the quinoxalinethiol f l aEd benzsthiazinethione 12. dium ethoxide t b g i v e the S-al&latedTroducta 2 urd 2 respectively.

The lactam quinoxalinone 3a, benzothiazinone 3b and benzothiazinone 3c

Compounds 11 and 12 were alkylated with iodomzhane and so-

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